Triethylamine → 3-amino-6-bromo-N'-(phenylcarbonyl)pyrazine-2-carbohydrazide

HRID 78585

Reaktionsgleichung

Reaktionsgleichung von HRID 78585
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[NH2:30][C:31]1[C:32]([C:38]([OH:40])=O)=[N:33][C:34]([Br:37])=[CH:35][N:36]=1.[C:41]([NH:49][NH2:50])(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CN(C=O)C.O>[NH2:30][C:31]1[C:32]([C:38]([NH:50][NH:49][C:41]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:48])=[O:40])=[N:33][C:34]([Br:37])=[CH:35][N:36]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 11955BenzoylhydrazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid

Produkt 1

HCID 594723553-amino-6-bromo-N'-(phenylcarbonyl)pyrazine-2-carbohydrazideAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

TBTU (22.09 g, 68.80 mmol) and triethylamine (4.642 g, 6.394 mL, 45.87 mmol) were added to a suspension of 3-amino-6-bromo-pyrazine-2-carboxylic acid (10 g, 45.87 mmol) and benzohydrazide (7.494 g, 55.04 mmol) in DMF (100.0 mL) and the resulting solution stirred at ambient temperature for 48 hours and then poured into water (400 mL) with vigorous stirring. This was allowed to stir for 30 minutes, filtered and washed with water. The moist solid was dissolved in hot EtOAc, dried (MgSO4), filtered and concentrated in vacuo and the resultant solid dried under vacuum to give the desired product (11.34 g, 73% Yield). 1H NMR (400.0 MHz, DMSO) d 7.51 (2H, m), 7.61 (1H, m), 7.69 (2H, br s), 7.92 (2H, m), 8.44 (1H, s), 10.48 (1H, br s), 10.54 (1H, br s) ppm; MS (ES+) 338.01

Aufarbeitung

  1. stirringto stir for 30 minutes
  2. filtrationfiltered
  3. washwashed with water
  4. dissolutionThe moist solid was dissolved in hot EtOAc
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe resultant solid dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-cd25e745e6ad4c6c8a4d53b81cbc2ae8
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841308B2

Verknüpfte Notizen

Wird geladen…